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Flat != empowered

I was the seventh hire at Pantheon (we’re over 95 now), and the day I started I was chomping at the bit to contribute and make a difference. I knew I had a lot to bring to the table, I knew what I wanted, and I just needed to be let loose, to start developing the technology that now serves 10s of billions page-views per month for some of the largest websites on the internet: educational institutions, non-profits, three-letter-acronym organizations, personal blogs, small businesses, and a half-dozen Pantheon employee wedding sites.

As we grew, and I thought about growing the engineering team, I wanted every new hire to bring that same conscious impactfulness. And they did. We started growing a dedicated and talented team, some homegrown at Pantheon and others with teeth cut at Twitter, Zynga, GoDaddy, TeraData, Lyft, Korea Telecom, Opscode, etc.

As the team grew past 8 and then past 15, I started adjusting my role to support the team. I was so excited about this feeling of impactfulness and reading just enough compelling literature, absorbing some Silicon Valley echo-chamber rumors about “no managers”, and bantering with some really coolcompanies genuinely trying to do things differently. Growing with a startup is incredibly energizing. So energizing that you might miss the fact that, as company of 20, you have as much in common with a pickup soccer team as the companies showing ads on Highway 101 billboards. Part of a startup’s role is to do things differently, but that doesn’t mean you should reinvent the wheel (in this case, the management wheel).

Somewhere along the line, amidst getting married, helping grow the Pantheon to over 95 people, celebrating birthdays and anniversaries resolving infrastructure issues on my macbook, I misconstrued my true goal of an empowered, impactful team as a ‘flat’ organization. After this association equating ‘flat’ with ‘empowered’ was set in my head, each additional person I was supporting in my management role was a +1 to Pantheon’s flatness, a feather-in-our-cap to our innovativeness. I didn’t realize I was also digging myself into managerial debt.

This continued for several months. I read Managing Humans and filled my calendar with 1-on-1s (except for that one employee, who thought that was weird, so we scheduled 1-to-1s). I traipsed across Chinatown on walk-n-talk 1-on-1s, asked how I could help, and got crap out of the way of the engineers. Easy, who wouldn’t love mgmt?

And then it happened. It probably wasn’t one single day, but it felt like that. The last straw. It might have been committing to org-wide performance reviews, or communicating a slight strategic adjustment, or a series of off-site speaking obligations. All of a sudden, I could not support my team. I wasn’t accessible, I was rescheduling or truncating 1-on-1s. I was deferring real questions until next-week’s meeting. I’m not sure how much my team felt it, but that’s when I knew I had messed up.

It took months to dig out of the managerial debt. Now, we have an amazing engineering management team. We believe that managers, good managers, truly help make every employee a stronger contributor to Pantheon and indeed a better person. (To put a # on it, supporting more than 8 engineers is accruing debt).

Empower your team, hire (great) managers, write up an org chart and flip it upside down. Don’t fear org charts, managers or Sales. Hire managers with EQ, nerds who dropped out of college, and build the team that you’d want to come in Sundays just to work with or reboot a few hundred production critical servers with on a few hours notice. Don’t confuse “flat” or “no managers” with a happy, productive team. I did once, but I won’t again.